Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR3479)
Drug Name
Sildenafil
Synonyms
sildenafil; 139755-83-2; VIAGRA; Sildenafil [INN:BAN]; UK-92480; UNII-3M7OB98Y7H; UK-92,480-10; C22H30N6O4S; HSDB 7305; CHEMBL192; UK 92480-10; CHEBI:9139; 3M7OB98Y7H; BNRNXUUZRGQAQC-UHFFFAOYSA-N; Sildenafil
Indication Erectile dysfunction [ICD11: HA00-HA01] Approved [1]
Coronavirus Disease 2019 (COVID-19) [ICD11: ICD11: 1D6Y] Phase 3 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 474.6 Topological Polar Surface Area 118
Heavy Atom Count 33 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
135398744
ChEBI ID
CHEBI:9139
CAS Number
139755-83-2
TTD Drug ID
D05ULR
Formula
C22H30N6O4S
Canonical SMILES
CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C
InChI
InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
InChIKey
BNRNXUUZRGQAQC-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
N-desmethyl Sildenafil DM001315
135455980
Unclear - Unclear 1 [3] , [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013895 Sildenafil N-desmethyl Sildenafil Unclear - Unclear CYP2D6 ... [3], [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
References
1 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 206401.
2 ClinicalTrials.gov (NCT04304313) A Pilot Study of Sildenafil in COVID-19. U.S. National Institutes of Health.
3 Functional Measurement of CYP2C9 and CYP3A4 Allelic Polymorphism on Sildenafil Metabolism
4 In vitro biotransformation of sildenafil (Viagra): identification of human cytochromes and potential drug interactions. Drug Metab Dispos. 2000 Apr;28(4):392-7.
5 Contribution of CYP3A isoforms to dealkylation of PDE5 inhibitors: a comparison between sildenafil N-demethylation and tadalafil demethylenation. Biol Pharm Bull. 2015;38(1):58-65.

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